Brivudine | BVDU | RP101 | CAS# 69304-47-8

MedKoo Cat#: 100103 | Name: Brivudine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Brivudine, also known as bromovinyl-deoxyuridine, is a uridine derivative and nucleoside analog with pro-apoptotic and chemosensitizing properties. In vitro, bromovinyl-deoxyuridine (BVDU) has been shown to downregulate the multifunctional DNA repair enzyme APEX nuclease 1, resulting in the inhibition of DNA repair and the induction of apoptosis. In addition, this agent may inhibit the expression of STAT3 (signal transducer and activator of transcription 3), which may result in the downregulation of vascular endothelial growth factor (VEGF). BVDU has also been found to inhibit the upregulation of chemoresistance genes (Mdr1 and DHFR) during chemotherapy.

Chemical Structure

Brivudine

CAS#69304-47-8 (free base)

Theoretical Analysis

MedKoo Cat#: 100103

Name: Brivudine

CAS#: 69304-47-8 (free base)

Chemical Formula: C11H13BrN2O5

Exact Mass: 332.0008

Molecular Weight: 333.13

Elemental Analysis: C, 39.66; H, 3.93; Br, 23.99; N, 8.41; O, 24.01

Price and Availability

Size	Price	Availability
50mg	USD 90.00	Ready to ship
100mg	USD 150.00	Ready to ship
200mg	USD 225.00	Ready to ship
500mg	USD 500.00	Ready to ship
1g	USD 850.00	Ready to ship
2g	USD 1,450.00	Ready to ship
5g	USD 3,050.00	Ready to ship

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Related CAS #

69304-47-8 (free base) 80860-82-8 (phosphate)

Synonym

Bridic; Brivox; Brivudin; Helpin ;Zerpex; Zonavir; and Zostex; BVDU; RP101; RP-101; RP 101;

IUPAC/Chemical Name

5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

InChi Key

ODZBBRURCPAEIQ-PIXDULNESA-N

InChi Code

InChI=1S/C11H13BrN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h1-2,4,7-9,15-16H,3,5H2,(H,13,17,18)/b2-1+/t7-,8+,9+/m0/s1

SMILES Code

O=C1NC(C(/C=C/Br)=CN1[C@@H]2O[C@H](CO)[C@@H](O)C2)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

According to http://en.wikipedia.org/wiki/Brivudine, Brivudine is approved for use in Germany and other European countries including Italy. Brivudine is a similar drug to acyclovir The compound was first synthesized by scientists at the University of Birmingham in the UK in the 1970s. It was shown to be a potent inhibitor of the herpes simplex virus Type 1 (HSV-1) as well as the varicella zoster virus (VZV) by Erik De Clercq at the Rega Institute for Medical Research in Belgium in 1979. In the 1980s the drug became commercially available in East Germany, where it was marketed as Helpin by a pharmaceutical company called Berlin-Chemie.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#TZC50309

QC Data

View QC data: current batch, Lot#TZC50309

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Brivudine is a thymidine analogue with antiviral activity.

In vitro activity:

RP101 binds in vitro to the heat shock protein HSPB1 and inhibits interaction with its binding partners. As a result, more activated CASP9 was detected in RP101-treated cancer cells. Reference: J Cancer Res Clin Oncol. 2011 Sep;137(9):1349-61. https://link.springer.com/article/10.1007%2Fs00432-011-1005-1

In vivo activity:

RP101 was tested as an anti-cancer drug in a rat model, and it was found that it improved chemotherapy. Reference: J Cancer Res Clin Oncol. 2011 Sep;137(9):1349-61. https://link.springer.com/article/10.1007%2Fs00432-011-1005-1

	Solvent	mg/mL	mM
Solubility
	DMSO	142.0	426.26
	DMF	30.0	90.05
	Ethanol	10.0	30.02
	PBS (pH 7.2)	0.5	1.50

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 333.13 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Heinrich JC, Tuukkanen A, Schroeder M, Fahrig T, Fahrig R. RP101 (brivudine) binds to heat shock protein HSP27 (HSPB1) and enhances survival in animals and pancreatic cancer patients. J Cancer Res Clin Oncol. 2011 Sep;137(9):1349-61. doi: 10.1007/s00432-011-1005-1. Epub 2011 Jul 22. PMID: 21833720.

In vitro protocol:

In vivo protocol:

1: Patil A, Goldust M, Wollina U. Herpes zoster: A Review of Clinical Manifestations and Management. Viruses. 2022 Jan 19;14(2):192. doi: 10.3390/v14020192. PMID: 35215786; PMCID: PMC8876683. 2: Rabasseda X. Brivudine: a herpes virostatic with rapid antiviral activity and once-daily dosing. Drugs Today (Barc). 2003 May;39(5):359-71. doi: 10.1358/dot.2003.39.5.740221. PMID: 12861349. 3: Andrei G, Snoeck R. Advances and Perspectives in the Management of Varicella- Zoster Virus Infections. Molecules. 2021 Feb 20;26(4):1132. doi: 10.3390/molecules26041132. PMID: 33672709; PMCID: PMC7924330. 4: Dworkin RH, Johnson RW, Breuer J, Gnann JW, Levin MJ, Backonja M, Betts RF, Gershon AA, Haanpaa ML, McKendrick MW, Nurmikko TJ, Oaklander AL, Oxman MN, Pavan-Langston D, Petersen KL, Rowbotham MC, Schmader KE, Stacey BR, Tyring SK, van Wijck AJ, Wallace MS, Wassilew SW, Whitley RJ. Recommendations for the management of herpes zoster. Clin Infect Dis. 2007 Jan 1;44 Suppl 1:S1-26. doi: 10.1086/510206. PMID: 17143845. 5: Collins SL, Patterson AD. The gut microbiome: an orchestrator of xenobiotic metabolism. Acta Pharm Sin B. 2020 Jan;10(1):19-32. doi: 10.1016/j.apsb.2019.12.001. Epub 2019 Dec 10. PMID: 31998605; PMCID: PMC6984741. 6: Vogel C, Wetzel L, Wutzler P, Gruhn B. Treatment with brivudine in immunocompromised pediatric patients with herpes zoster. Chemotherapy. 2023 May 18. doi: 10.1159/000531034. Epub ahead of print. PMID: 37231819. 7: Drositis I, Kontopodis E, Saloustros E, Androulakis N. Interaction of brivudine with capecitabine: A case of serious toxicity. J BUON. 2019 Nov- Dec;24(6):2579. PMID: 31983140. 8: García Herrera AN, Moncayola Vicén JC. Interacción mortal entre 5-fluorouracilo y brivudina [Lethal interaction between 5-fluorouracil and brivudine]. An Sist Sanit Navar. 2018 Aug 29;41(2):277-278. Spanish. doi: 10.23938/ASSN.0297. PMID: 29943764. 9: Buturak A, Norgaz T, Gorgulu S. Brivudine induced coronary vasospasm as a manifestation of Kounis syndrome: First report. Int J Cardiol. 2015 Apr 15;185:4-6. doi: 10.1016/j.ijcard.2015.03.082. Epub 2015 Mar 10. PMID: 25777280. 10: Zimmermann M, Zimmermann-Kogadeeva M, Wegmann R, Goodman AL. Separating host and microbiome contributions to drug pharmacokinetics and toxicity. Science. 2019 Feb 8;363(6427):eaat9931. doi: 10.1126/science.aat9931. Epub 2019 Feb 7. PMID: 30733391; PMCID: PMC6533120. 11: Heinrich JC, Tuukkanen A, Schroeder M, Fahrig T, Fahrig R. RP101 (brivudine) binds to heat shock protein HSP27 (HSPB1) and enhances survival in animals and pancreatic cancer patients. J Cancer Res Clin Oncol. 2011 Sep;137(9):1349-61. doi: 10.1007/s00432-011-1005-1. Epub 2011 Jul 22. PMID: 21833720. 12: Tsifi A, Papaxoinis G, Diamantopoulos P, Mantzourani M, Antoniadou V, Halioti A, Gogas H. A life-threatening drug-drug interaction between capecitabine and brivudine in a patient with metastatic breast cancer. J Chemother. 2019 Nov-Dec;31(7-8):424-427. doi: 10.1080/1120009X.2019.1665875. Epub 2019 Sep 13. PMID: 31516092. 13: Yaldiz M, Solak B, Kara RO, Cosansu N, Erdem MT. Comparison of Famciclovir, Valaciclovir, and Brivudine Treatments in Adult Immunocompetent Patients With Herpes Zoster. Am J Ther. 2018 Nov/Dec;25(6):e626-e634. doi: 10.1097/MJT.0000000000000436. PMID: 26808358. 14: De Clercq E. Selective anti-herpesvirus agents. Antivir Chem Chemother. 2013 Jan 23;23(3):93-101. doi: 10.3851/IMP2533. PMID: 23343513. 15: De Clercq E. The development of BVDU: An odyssey. Antivir Chem Chemother. 2023 Jan-Dec;31:20402066231152971. doi: 10.1177/20402066231152971. PMID: 36710501; PMCID: PMC9902897. 16: Vij O, Bornfeld N, Roggendorf M, Fiedler M, Schilling H. Brivudin als alternative systemische Therapie zu Aciclovir und Ganciclovir bei akutem retinalen Nekrosesyndrom durch Varizella-Zoster-Virus [Brivudine as an alternative systemic therapy to aciclovir and ganciclovir in acute retinal necrosis syndrome due to varicella-zoster virus]. Klin Monbl Augenheilkd. 2003 Oct;220(10):710-5. German. doi: 10.1055/s-2003-43138. PMID: 14577039. 17: Lou Z, Post A, Rodgers CE, Chamankhah M, Hong J, Ahuja CS, Khazaei M, Fehlings MG. Neural Progenitor Cells Expressing Herpes Simplex Virus-Thymidine Kinase for Ablation Have Differential Chemosensitivity to Brivudine and Ganciclovir. Front Cell Neurosci. 2021 Dec 6;15:638021. doi: 10.3389/fncel.2021.638021. PMID: 34938162; PMCID: PMC8685296. 18: Baena Cañada JM, Martínez-Bautista MJ, Cortés-Carmona C, González-Carrascosa Vega T. Interacción farmacológica no mortal entre capecitabina y brivudina [Non- fatal drug-drug interaction between capecitabine and brivudine]. Farm Hosp. 2013 Jul-Aug;37(4):342-3. Spanish. doi: 10.7399/FH.2013.37.4.694. PMID: 24010699. 19: White DO. Antiviral chemotherapy. Med J Aust. 1984 Jun 9;140(12):715-20. doi: 10.5694/j.1326-5377.1984.tb108360.x. PMID: 6203021. 20: Rätz Bravo AE, Hofer S, Krähenbühl S, Ludwig C. Fatal drug-drug interaction of brivudine and capecitabine. Acta Oncol. 2009;48(4):631-3. doi: 10.1080/02841860802660502. PMID: 19165642.